Go To Lawyers: Jessica G. Kelly
Partner, Freeman, Mathis & Gary, Boston
Mass. Lawyers Weekly Staff//October 6, 2025//
Years in practice:
19
Best known for:
Defending lawyers and law firms in legal malpractice and bar disciplinary matters. I also represent real estate professionals and accountants in professional negligence cases and have a general commercial litigation practice.
Why I chose my practice area:
I had the good fortune to learn from exceptional mentors like Tom Maffei, Judge Debra Squires-Lee, and Bob Muldoon at Sherin & Lodgen, and later Nancy Reimer at Freeman, Mathis & Gary. I find meaning and purpose in defending people’s reputations and characters.
Most memorable case:
Trying a legal malpractice case with Bob Muldoon — his last trial before retirement — taught me about developing narrative and commanding a courtroom. I also remember a Franklin County trial with Sara Shanahan and Elizabeth Rice, living in Greenfield hotel rooms during the intense, unscripted reality of jury trial preparation.
What makes me a leader in my field:
At almost 20 years into my career, I feel confident in my abilities. Legal malpractice cases require constantly learning new practice areas and creative approaches to resolution. Leadership requires empathy — I provide steady guidance for clients experiencing the difficult process of being accused of mistakes.
Outlook for 2025:
Professional liability issues involving artificial intelligence will dominate the next few years. Courts are regularly sanctioning attorneys for improper AI use, yet lawyers must be competent with technology. We’re approaching a standard of care requiring proper and responsible AI use in legal practice.
Bar involvement/leadership roles:
Vice chair of the professional liability practice group and chair of the lawyer’s group at my firm. Former vice chair and chair of the Complex Commercial Litigation Section Council at the Massachusetts Bar Association.
Representative clients:
I represent lawyers at big firms, small firms and solo practitioners.
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